Heterocyclic compound and organic light emitting device using the same

ABSTRACT

The present specification provides a heterocyclic compound, and an organic light emitting device including: a first electrode, a second electrode, and organic material layers formed of one or more layers including a light emitting layer disposed between the first electrode and the second electrode, in which one or more layers of the organic material layers include the heterocyclic compound or a compound in which a heat-curable or photo-curable functional group is introduced into the heterocyclic compound.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to and the benefit of Korean PatentApplication No. 10-2013-0013868 filed in the Korean IntellectualProperty Office on Feb. 7, 2013, the entire contents of which areincorporated herein by reference.

TECHNICAL FIELD

The present specification relates to a heterocyclic compound and anorganic light emitting device using the same.

BACKGROUND ART

An organic light emitting phenomenon is an example of converting acurrent into visible rays by an internal process of a specific organicmolecule. The organic light emitting phenomenon is based on thefollowing principle.

When an organic material layer is positioned between an anode and acathode, if a voltage is applied between two electrodes, electrons andholes are injected from the cathode and the anode into the organicmaterial layer. The electrons and the holes injected into the organicmaterial layer are recombined to form an exciton, and the exciton isreduced again to a bottom state to emit light. In general, an organiclight emitting device using this principle may be constituted by acathode, an anode, and an organic material layer positionedtherebetween, for example, an organic material layer including a holeinjection layer, a hole transport layer, a light emitting layer, and anelectron transport layer.

A material used in the organic light emitting device is mostly a pureorganic material or a complex compound where an organic material andmetal form a complex, and may be classified into a hole injectionmaterial, a hole transport material, a light emitting material, anelectron transport material, an electron injection material, and thelike according to the purpose thereof. Herein, an organic materialhaving a p-type property, that is, an organic material that is easilyoxidized and has an electrochemically stable state during oxidation, ismostly used as the hole injection material or the hole transportmaterial. Meanwhile, an organic material having an n-type property, thatis, an organic material that is easily reduced and has anelectrochemically stable state during reduction, is mostly used as theelectron injection material or the electron transport material. Amaterial having both p-type and n-type properties, that is, a materialhaving a stable form in both oxidation and reduction states, may be usedas the light emitting layer material, and a material having high lightemitting efficiency for conversion of the exciton into light when theexciton is formed is preferable.

Accordingly, there is a demand to develop a novel organic material inthe art.

SUMMARY OF THE INVENTION

The present specification has been made in an effort to provide aheterocyclic compound and an organic light emitting device using thesame.

An exemplary embodiment of the present specification provides a compoundrepresented by the following Chemical Formula 1 or 2.

wherein a is an integer of 0 to 7,

b is an integer of 0 to 4,

c is an integer of 0 to 8,

d is an integer of 0 to 5,

A₁ to A₈ are the same as or different from each other and are eachindependently CR or N, but two or more of A₁ to A₈ are N, and

R and R₁ to R₄ are the same as or different from each other, and areeach independently hydrogen; deuterium; a halogen group; a nitrilegroup; a nitro group; a hydroxy group; a carbonyl group; an ester group;an imide group; an amide group; a substituted or unsubstituted alkylgroup; a substituted or unsubstituted cycloalkyl group; a substituted orunsubstituted alkoxy group; a substituted or unsubstituted aryloxygroup; a substituted or unsubstituted alkylthioxy group; a substitutedor unsubstituted arylthioxy group; a substituted or unsubstitutedalkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted silyl group; a substituted or unsubstituted boron group; asubstituted or unsubstituted alkylamine group; a substituted orunsubstituted aralkylamine group; a substituted or unsubstitutedarylamine group; a substituted or unsubstituted heteroarylamine group; asubstituted or unsubstituted arylphosphine group; a substituted orunsubstituted phosphine oxide group; a substituted or unsubstituted arylgroup; or a substituted or unsubstituted heterocyclic group includingone or more of N, O, and S atoms.

Another exemplary embodiment of the present specification provides anorganic light emitting device including: a first electrode, a secondelectrode, and organic material layers of one or more layers disposedbetween the first electrode and the second electrode, in which one ormore layers of the organic material layers include the heterocycliccompound represented by Chemical Formula 1 or 2 or a compound in which aheat-curable or photo-curable functional group is introduced into theheterocyclic compound.

The heterocyclic compound according to the exemplary embodiment of thepresent specification has an appropriate energy level and excellentelectrochemical stability and thermal stability. Accordingly, an organiclight emitting device including the compound provides high efficiencyand/or high driving stability.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates an example of an organic light emitting deviceincluding a substrate 1, an anode 2, a light emitting layer 3, and acathode 4.

FIG. 2 illustrates an example of an organic light emitting deviceincluding a substrate 1, an anode 2, a hole injection layer 5, a holetransport layer 6, a light emitting layer 7, an electron transport layer8, and a cathode 4.

FIG. 3 is a view illustrating an MS spectrum of Structural Formula A-1prepared in Preparation Example 1.

FIG. 4 is a view illustrating an MS spectrum of Chemical Formula 1-3prepared in Preparation Example 1.

DETAILED DESCRIPTION

Hereinafter, the present invention will be described in detail.

In an exemplary embodiment of the present specification, there isprovided a compound represented by Chemical Formula 1.

In the exemplary embodiment of the present specification, there isprovided a compound represented by Chemical Formula 2.

An organic light emitting device including the heterocyclic compoundaccording to the exemplary embodiment of the present specification mayhave an effect of a driving voltage reduction and/or an efficiencyincrease.

Examples of substituent groups will be described below, but are notlimited thereto.

In the present specification, examples of a halogen group includefluorine, chlorine, bromine, or iodine.

In the present specification, oxygen of an ester group may besubstituted with a straight-chained, branched-chained, or cyclic-chainedalkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25carbon atoms. Specifically, the ester group may be compounds having thefollowing Structural Formulas, but is not limited thereto.

In the present specification, the number of carbon atoms of an imidegroup is not particularly limited but is preferably 1 to 25.Specifically, the imide group may be compounds having the followingstructures, but is not limited thereto.

In the present specification, one or two nitrogen atoms of an amidegroup may be substituted with hydrogen, a straight-chained,branched-chained, or cyclic-chained alkyl group having 1 to 25 carbonatoms, or an aryl group having 6 to 25 carbon atoms. Specifically, theamide group may be compounds having the following Structural Formulas,but is not limited thereto.

In the present specification, the alkyl group may be a straight orbranched chain, and the number of carbon atoms thereof is notparticularly limited but is preferably 1 to 50. Specific examplesthereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl,n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl,pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl,1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl,2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl,cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl,2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl,1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl,4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, a cycloalkyl group is not particularlylimited, but the number of carbon atoms thereof is preferably 3 to 60,and the cycloalkyl group may have a monocycle or a polycycle. Specificexamples thereof include cyclopropyl, cyclobutyl, cyclopentyl,3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl,3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl,3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl,cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be a straight,branched, or cyclic chain. The number of carbon atoms of the alkoxygroup is not particularly limited, but preferably 1 to 20. Specificexamples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy,i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy,neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy,2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy,p-methylbenzyloxy, and the like, but are not limited thereto.

In the present specification, the aryl group is an organic radicalderived from aromatic hydrocarbons by removing one hydrogen, and mayhave a monocycle or a polycycle. The number of carbon atoms of the arylgroup is not particularly limited, but preferably 6 to 60. Specificexamples of the aryl group include monocyclic aromatics such as a phenylgroup, a biphenyl group, a triphenyl group, a terphenyl group, and astilbene group, polycyclic aromatics such as a naphthyl group, ananthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenylgroup, a tetracenyl group, a chrysenyl group, a fluorenyl group, anacenaphthacenyl group, a triphenylene group, and a fluoranthene group,and the like, but are not limited thereto.

In the present specification, the fluorenyl group has a structure wheretwo cyclic organic compounds are connected through one atom, andexamples thereof include

and the like.

In the present specification, the fluorenyl group includes a structureof an opened fluorenyl group, herein, the opened fluorenyl group has astructure where two cyclic compounds are connected through one atom andconnection of one cyclic compound is broken, and examples thereofinclude

and the like.

In the present specification, the heterocyclic group is a heterocyclicgroup including O, N, or S as a heteroatom, and the number of carbonatoms thereof is not particularly limited, but is preferably 2 to 60.Examples of the heterocyclic group include a thiophene group, a furangroup, a pyrrole group, an imidazole group, a thiazole group, an oxazolgroup, an oxadiazol group, a triazol group, a pyridyl group, a bipyridylgroup, a pyrimidyl group, a triazine group, a triazole group, an acridylgroup, a pyridazine group, a pyrazinyl group, a quinolinyl group, aquinazoline group, a quinoxalinyl group, a phthalazinyl group, apyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinylgroup, an isoquinoline group, an indole group, a carbazole group, abenzoxazole group, a benzoimidazole group, a benzothiazol group, abenzocarbazole group, a benzothiophene group, a dibenzothiophene group,a benzofuranyl group, a phenanthroline group, a thiazolyl group, anisoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, abenzothiazolyl group, a phenothiazinyl group, a dibenzofuranyl group,and the like, but are not limited thereto.

In the present specification, the aryl group of an aryloxy group, anarylthioxy group, an arylsulfoxy group, and an aralkylamine group is thesame as the aforementioned examples of the aryl group. Specific examplesof the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy,3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy,3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy,4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy,2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy,9-phenanthryloxy, and the like, specific examples of the arylthioxygroup include a phenylthioxy group, a 2-methylphenylthioxy group, a4-tert-butylphenylthioxy group, and the like, and specific examples ofthe arylsulfoxy group include a benzenesulfoxy group, a p-toluenesulfoxygroup, and the like, but the examples are not limited thereto.

In the present specification, the alkyl group of an alkylthioxy groupand an alkylsulfoxy group is the same as the aforementioned examples ofthe alkyl group. Specific examples of the alkylthioxy group include amethylthioxy group, an ethylthioxy group, a tert-butylthioxy group, ahexylthioxy group, an octylthioxy group, and the like, and specificexamples of the alkylsulfoxy group include mesyl, an ethylsulfoxy group,a propylsulfoxy group, a butylsulfoxy group, and the like, but theexamples are not limited thereto.

In the present specification, a heteroaryl group of a heteroarylaminegroup may be selected from the aforementioned examples of theheterocyclic group.

In the present specification, specific examples of an aralkyl group ofthe aralkylamine group include a benzyl group, a p-methylbenzyl group,an m-methylbenzyl group, a p-ethylbenzyl group, an m-ethylbenzyl group,a 3,5-dimethylbenzyl group, an α-methylbenzyl group, anα,α-dimethylbenzyl group, an α,α-methylphenylbenzyl group, a1-naphthylbenzyl group, a 2-naphthylbenzyl group, a p-fluorobenzylgroup, a 3,5-difluorobenzyl group, an α,α-ditrifluoromethylbenzyl group,a p-methoxybenzyl group, an m-methoxybenzyl group, an α-phenoxybenzylgroup, an α-benzyloxybenzyl group, a naphthylmethyl group, anaphthylethyl group, a naphthylisopropyl group, a pyrrolylmethyl group,a pyrrolelethyl group, an aminobenzyl group, a nitrobenzyl group, acyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a1-chloro-2-phenylisopropyl group, and the like, but are not limitedthereto.

In the present specification, the alkenyl group may be a straight orbranched chain, and the number of carbon atoms thereof is notparticularly limited but is preferably 2 to 40. Specific examplesthereof include vinyl, 1-prophenyl, isoprophenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl,1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl,2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl,2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl group,and the like, but are not limited thereto.

In the present specification, specific examples of the silyl groupinclude a trimethylsilyl group, a triethylsilyl group, at-butyldimethylsilyl group, a vinyldimethylsilyl group, apropyldimethylsilyl group, a triphenylsilyl group, a diphenylsilylgroup, a phenylsilyl group, and the like, but are not limited thereto.

In the present specification, the number of carbon atoms of an aminegroup is not particularly limited, but preferably 1 to 30. Specificexamples of the amine group include a methylamine group, a dimethylaminegroup, an ethylamine group, a diethylamine group, a phenylamine group, anaphthylamine group, a biphenylamine group, an anthracenylamine group, a9-methyl-anthracenylamine group, a diphenylamine group, aphenylnaphthylamine group, a ditolylamine group, a phenyltolylaminegroup, a triphenylamine group, and the like, but are not limitedthereto.

In the present specification, examples of an arylamine group include asubstituted or unsubstituted monoarylamine group, a substituted orunsubstituted diarylamine group, or a substituted or unsubstitutedtriarylamine group. The aryl group of the arylamine group may be amonocyclic aryl group or a polycyclic aryl group. The arylamine groupincluding two or more aryl groups may include the monocyclic aryl group,the polycyclic aryl group, or both the monocyclic aryl group and thepolycyclic aryl group.

Specific examples of the arylamine group include phenylamine,naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine,4-methyl-naphthylamine, 2-methyl-biphenylamine,9-methyl-anthracenylamine, a diphenylamine group, a phenylnaphthylaminegroup, a ditolylamine group, a phenyltolylamine group, carbazole, atriphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of an arylphosphine group includea substituted or unsubstituted monoarylphosphine group, a substituted orunsubstituted diarylphosphine group, or a substituted or unsubstitutedtriarylphosphine group. The aryl group of the arylphosphine group may bea monocyclic aryl group or a polycyclic aryl group. The arylphosphinegroup including two or more aryl groups may include the monocyclic arylgroup, the polycyclic aryl group, or both the monocyclic aryl group andthe polycyclic aryl group.

Further, in the present specification, the term “substituted orunsubstituted” means that substitution is performed by one or moresubstituent groups selected from the group consisting of deuterium; ahalogen group; an alkyl group; an alkenyl group; an alkoxy group; acycloalkyl group; a silyl group; an arylalkenyl group; an aryl group; anaryloxy group; an alkylthioxy group; an alkylsulfoxy group; anarylsulfoxy group; a boron group; an alkylamine group; an aralkylaminegroup; an arylamine group; a heteroaryl group; a carbazole group; anarylamine group; an aryl group; a fluorenyl group; a nitrile group; anitro group; a hydroxy group; and a heterocyclic group including one ormore of N, O, and S atoms, or there is no substituent group, and thesubstituent groups may be further substituted or unsubstituted.

The term “substituted” means that a hydrogen atom bonded to a carbonatom of a compound is changed into another substituent group, asubstitution position is not limited as long as the substitutionposition is a position at which the hydrogen atom is substituted, thatis, a position at which the substituent group can be substituted, and inthe case where two or more atoms are substituted, two or moresubstituent groups may be the same as or different from each other.

In the exemplary embodiment of the present specification, at least twoof A₁ to A₈ are N.

In the exemplary embodiment of the present specification, at least oneof A₁ to A₄ is N.

In the exemplary embodiment of the present specification, at least twoof A₁ to A₄ are N.

In the exemplary embodiment of the present specification, at least oneof A₅ to A₈ is N.

In the exemplary embodiment of the present specification, at least twoof A₅ to A₈ are N.

In the exemplary embodiment of the present specification, A₅ is N.

In the exemplary embodiment of the present specification, A₆ is N.

In the exemplary embodiment of the present specification, A₇ is N.

In the exemplary embodiment of the present specification, A₈ is N.

In the exemplary embodiment of the present specification, A₅ and A₇ areN.

In the exemplary embodiment of the present specification, A₆ and A₈ areN.

In the exemplary embodiment of the present specification, A₅ is CR.

In the exemplary embodiment of the present specification, A₆ is CR.

In the exemplary embodiment of the present specification, A₇ is CR.

In the exemplary embodiment of the present specification, A₈ is CR.

In the exemplary embodiment of the present specification, A₅ and A₇ areN, A₆ and A₈ are CR or A₆ and A₈ are N, and A₅ and A₇ are CR.

In the exemplary embodiment of the present specification, A₅ and A₇ areN and A₆ is CR.

In the exemplary embodiment of the present specification, A₅ and A₇ areN, A₆ is CR, and A₈ is CR.

In the exemplary embodiment of the present specification, A₆ and A₈ areN and A₇ is CR.

In the exemplary embodiment of the present specification, A₆ and A₈ areN, A₇ is CR, and A₅ is CH.

In the exemplary embodiment of the present specification, A₆ and A₈ areN, A₇ is CR, and A₅ is CR.

In the exemplary embodiment of the present specification, R is hydrogen;a substituted or unsubstituted aryl group; or a substituted orunsubstituted heterocyclic group including one or more of substituted orunsubstituted N, O, and S atoms.

In another exemplary embodiment, R is hydrogen; an aryl groupunsubstituted or substituted with one or two or more substituent groupsselected from the group consisting of a substituted or unsubstitutedphosphine oxide group, a substituted or unsubstituted aryl group, and asubstituted or unsubstituted heterocyclic group including one or more ofN, O, and S atoms; or a heterocyclic group including one or more of N,O, and S atoms unsubstituted or substituted with one or two or moresubstituent groups selected from the group consisting of a substitutedor unsubstituted phosphine oxide group, a substituted or unsubstitutedaryl group, and a substituted or unsubstituted heterocyclic groupincluding one or more of N, O, and S atoms.

In the exemplary embodiment of the present specification, R is hydrogen;a phenyl group unsubstituted or substituted with a substituent groupselected from the group consisting of a phenyl group, a phosphine oxidegroup substituted with a phenyl group, a triazine group, and apyrimidine group; a naphthyl group unsubstituted or substituted with asubstituent group selected from the group consisting of a phenyl group,a phosphine oxide group substituted with a phenyl group, a triazinegroup, and a pyrimidine group; a biphenyl group unsubstituted orsubstituted with a substituent group selected from the group consistingof a phenyl group, a phosphine oxide group substituted with a phenylgroup, a triazine group, and a pyrimidine group; or a pyridine groupunsubstituted or substituted with a substituent group selected from thegroup consisting of a phenyl group, a phosphine oxide group substitutedwith a phenyl group, a triazine group, and a pyrimidine group.

In the exemplary embodiment of the present specification, R is hydrogen;a phenyl group unsubstituted or substituted with a substituent groupselected from the group consisting of a phenyl group, a phosphine oxidegroup substituted with a phenyl group, a triazine group, and apyrimidine group; a naphthyl group; a biphenyl group unsubstituted orsubstituted with a phosphine oxide group substituted with a phenylgroup; or a pyridine group.

In the exemplary embodiment of the present specification, R is hydrogen.

In the exemplary embodiment of the present specification, R is asubstituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R is asubstituted or unsubstituted phenyl group.

In the exemplary embodiment of the present specification, R is a phenylgroup.

In the exemplary embodiment of the present specification, R is a phenylgroup substituted with a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R is a phenylgroup unsubstituted or substituted with a phenyl group.

In the exemplary embodiment of the present specification, R is a phenylgroup substituted with a substituted or unsubstituted phosphine oxidegroup.

In another exemplary embodiment, R is a phenyl group substituted with aphosphine oxide group substituted with an aryl group.

In the exemplary embodiment of the present specification, R is a phenylgroup substituted with a phosphine oxide group substituted with a phenylgroup.

In the exemplary embodiment of the present specification, R is a phenylgroup substituted with a substituted or unsubstituted heterocyclic groupincluding one or more of N, O, and S atoms.

In another exemplary embodiment, R is a phenyl group substituted with asubstituted or unsubstituted heterocyclic group including N.

In one exemplary embodiment, R is a phenyl group substituted with asubstituted or unsubstituted triazine group.

In another exemplary embodiment, R is a phenyl group substituted with atriazine group substituted with a phenyl group.

In the exemplary embodiment of the present specification, R is a phenylgroup substituted with a substituted or unsubstituted pyrimidine group.

In another exemplary embodiment, R is a phenyl group substituted with apyrimidine group unsubstituted or substituted with a phenyl group.

In the exemplary embodiment of the present specification, the pyrimidinegroup is

and may be unsubstituted or substituted with an additional substituentgroup.

In the exemplary embodiment of the present specification, R is asubstituted or unsubstituted naphthyl group.

In another exemplary embodiment, R is a naphthyl group.

In another exemplary embodiment, R is a substituted or unsubstitutedbiphenyl group.

In another exemplary embodiment, R is a biphenyl group.

In the exemplary embodiment of the present specification, R is abiphenyl group substituted with a substituted or unsubstituted phosphineoxide group.

In another exemplary embodiment, R is a biphenyl group substituted witha phosphine oxide group substituted with an aryl group.

In the exemplary embodiment of the present specification, R is abiphenyl group substituted with a phosphine oxide group substituted witha phenyl group.

In the exemplary embodiment of the present specification, R is asubstituted or unsubstituted heterocyclic group including one or more ofN, O, and S atoms.

In another exemplary embodiment, R is a substituted or unsubstitutedheterocyclic group including one or more N atoms.

In another exemplary embodiment, R is a substituted or unsubstitutedpyridine group.

In the exemplary embodiment of the present specification, the pyridinegroup is

In the exemplary embodiment of the present specification, R₁ ishydrogen.

In another exemplary embodiment, R₂ is hydrogen.

In one exemplary embodiment, R₃ is hydrogen.

In another exemplary embodiment, R₄ is hydrogen.

In the exemplary embodiment of the present specification, theheterocyclic compound represented by Chemical Formula 1 is representedby any one of the following Chemical Formulas 1-1 to 1-36.

In the exemplary embodiment of the present specification, theheterocyclic compound represented by Chemical Formula 2 is representedby any one of the following Chemical Formulas 2-1 to 2-32.

The heterocyclic compound of Chemical Formula 1 or 2 may be preparedbased on Preparation Examples as will be described later.

In the exemplary embodiment of the present specification, theheterocyclic compound represented by Chemical Formula 1 as well asChemical Formulas 1-1 to 1-36 may be prepared by reacting indenopyrimidi-5-on substituted with R with 9-(2-bromophenyl)-carbazole andperforming a ring-closing reaction.

In the exemplary embodiment of the present specification, theheterocyclic compound represented by Chemical Formula 2 as well asChemical Formulas 2-1 to 2-32 may be prepared by reacting indenopyrimidi-5-on substituted with R with 2-bromo-diphenylaniline andperforming a ring-closing reaction.

In the exemplary embodiment of the present specification, the compoundof Chemical Formula 1 or 2 includes a core structure in whichheterocyclic groups obtained by condensation of two 3-membered cycles orcondensation of a 3-membered cycle and a 5-membered cycle based oncarbon are bonded in a spiro structure.

In the exemplary embodiment of the present specification, the compoundof Chemical Formula 1 includes a core structure in which a substitutedor unsubstituted indenopyrimidine group and a substituted orunsubstituted acrydine group are bonded in a spiro structure.

The compound of Chemical Formula 1 or 2 has a property suitable to beused as an organic material layer used in an organic light emittingdevice by introducing various substituents to the core structurerepresented in Chemical Formula 1 or Chemical Formula 2.

In the exemplary embodiment of the present specification, a core of thecompound of Chemical Formula 1 or 2 limits conjugation between theheterocyclic groups in which the two 3-membered cycles are condensed orthe 3-membered cycle and the 5-membered cycle are condensed based oncarbon, which are subjected to spiro bonding.

A conjugation length of the compound has a close relationship with anenergy band gap. Specifically, the energy band gap is reduced as theconjugation length of the compound increases. As described above, sincethe core of the compound of Chemical Formula 1 or Chemical Formula 2includes a limited conjugation, the core has a property of a largeenergy band gap.

In the present specification, as described above, the compound havingvarious energy band gaps may be synthesized by introducing varioussubstituent groups to positions of R, and R₁ to R₄ of the core structurehaving the large energy band gap. Since the compound of Chemical Formula1 or Chemical Formula 2 according to the exemplary embodiment of thepresent specification has the large energy band gap, it is easy toadjust the energy band gap by introducing the substituent group.

Further, in the present specification, HOMO and LUMO energy levels ofthe compound may be adjusted by introducing various substituent groupsto the positions of R, and R₁ to R₄ of the core structure which is thesame as that described above.

Accordingly, the organic light emitting device including the compound ofChemical Formula 1 or Chemical Formula 2 according to the exemplaryembodiment of the present specification may provide an organic lightemitting device having high efficiency and a long life-span.

Further, compounds having intrinsic properties of the introducedsubstituent groups may be synthesized by introducing various substituentgroups to the core structure which is the same as that described above.For example, a material satisfying conditions required in each organicmaterial layer may be synthesized by introducing the substituent groupmainly used in a hole injection layer material, a hole transportmaterial, a light emitting layer material, and an electron transportlayer material used to manufacture the organic light emitting device tothe core structure.

The heterocyclic compound of Chemical Formula 1 or Chemical Formula 2according to the exemplary embodiment of the present specification hasappropriate hole or electron mobility. Accordingly, in the case wherethe heterocyclic compound is applied to the organic light emittingdevice, densities of holes and electrons may be allowed to be balancedin a light emitting layer to maximize formation of excitons.

The heterocyclic compound of Chemical Formula 1 or Chemical Formula 2according to the exemplary embodiment of the present specification hasan excellent interfacial property with the adjacent layer, and thus hasa merit in that stability of the device is high.

The heterocyclic compound of Chemical Formula 1 or Chemical Formula 2according to the exemplary embodiment of the present specification has ahigh glass transition temperature (T_(g)), and thus has excellentthermal stability. Such an increase in thermal stability becomes animportant factor providing driving stability to the device.

Further, the present specification provides an organic light emittingdevice using the compound of Chemical Formula 1 or Chemical Formula 2.

There is provided the organic light emitting device including a firstelectrode, a second electrode, and organic material layers formed of oneor more layers including a light emitting layer disposed between thefirst electrode and the second electrode, in which one or more layers ofthe organic material layers include the heterocyclic compound or acompound in which a heat-curable or photo-curable functional group isintroduced into the heterocyclic compound.

In the exemplary embodiment of the present specification, the organicmaterial layer includes a hole transport layer, a hole injection layer,or a layer where both the hole transporting and the hole injection areperformed, and the hole transport layer, the hole injection layer, orthe layer where both hole transporting and hole injection are performedincludes the heterocyclic compound or the compound in which theheat-curable or photo-curable functional group is introduced into theheterocyclic compound.

In the exemplary embodiment of the present specification, the lightemitting layer includes the heterocyclic compound or the compound inwhich the heat-curable or photo-curable functional group is introducedinto the heterocyclic compound.

In the exemplary embodiment of the present specification, the organicmaterial layer includes the heterocyclic compound or the compound inwhich the heat-curable or photo-curable functional group is introducedinto the heterocyclic compound as a host.

In the exemplary embodiment of the present specification, the organicmaterial layer includes the heterocyclic compound or the compound inwhich the heat-curable or photo-curable functional group is introducedinto the heterocyclic compound as the host, and another organiccompound, a metal, or a metal compound as a dopant.

In the exemplary embodiment of the present specification, the organicmaterial layer includes the light emitting layer, and the heterocycliccompound or the compound in which the heat-curable or photo-curablefunctional group is introduced into the heterocyclic compound as a hostof the light emitting layer.

In another exemplary embodiment, the heterocyclic compound or thecompound in which the heat-curable or photo-curable functional group isintroduced into the heterocyclic compound is included as the host of thelight emitting layer, and the organic compound, the metal, or the metalcompound is included as the dopant.

In the exemplary embodiment of the present specification, the organicmaterial layer includes an electron transport layer, and the electrontransport layer includes the heterocyclic compound or the compound inwhich the heat-curable or photo-curable functional group is introducedinto the heterocyclic compound.

In the exemplary embodiment of the present specification, the organicmaterial layer includes an electron injection layer, and the electroninjection layer includes the heterocyclic compound or the compound inwhich the heat-curable or photo-curable functional group is introducedinto the heterocyclic compound.

In the exemplary embodiment of the present specification, the organicmaterial layer includes the layer where both the electron injection andthe electron transporting are performed, and the layer where bothelectron injection and electron transporting are performed includes theheterocyclic compound or the compound in which the heat-curable orphoto-curable functional group is introduced into the heterocycliccompound.

In the exemplary embodiment of the present specification, theheterocyclic compound is included in the light emitting layer and/or theelectron transport layer.

In the organic light emitting device of the present specification, thecompound in which the heat-curable or photo-curable functional group isintroduced into the compound of Chemical Formula 1 or Chemical Formula 2may be used instead of the compound of Chemical Formula 1 or ChemicalFormula 2. The compound may be formed into the organic material layer bya method of forming a thin film by a solution coating method and thencuring the thin film when the device is manufactured while maintainingbasic physical properties of the compound of Chemical Formula 1 orChemical Formula 2.

In the exemplary embodiment of the present specification, theheat-curable or photo-curable functional group is a vinyl group or anacryl group.

In the exemplary embodiment of the present specification, the organicmaterial layer further includes one layer or two or more layers selectedfrom the group consisting of the hole injection layer, the holetransport layer, the electron transport layer, the electron injectionlayer, an electron blocking layer, and a hole blocking layer.

The organic material layer of the organic light emitting device of thepresent specification may have a single layer structure, or amultilayered structure in which two or more organic material layers arelaminated. For example, the organic light emitting device of the presentspecification may have a structure including the hole injection layer,the hole transport layer, the light emitting layer, the electrontransport layer, the electron injection layer, or the like as theorganic material layer. However, the structure of the organic lightemitting device is not limited thereto, but may include a smaller numberof organic layers.

In another exemplary embodiment, the organic light emitting device maybe an organic light emitting device having a structure (normal type)where an anode, organic material layers of one or more layers, and acathode are sequentially laminated on a substrate.

In another exemplary embodiment, the organic light emitting device maybe an organic light emitting device having an inverted directionstructure (inverted type) where the cathode, the organic material layersof one or more layers, and the anode are sequentially laminated on thesubstrate.

In the exemplary embodiment of the present specification, the firstelectrode is the cathode, and the second electrode is the anode. Inanother exemplary embodiment, the first electrode is the anode, and thesecond electrode is the cathode.

The structure of the organic light emitting device of the presentspecification is illustrated in FIGS. 1 and 2, but is not limitedthereto.

FIG. 1 illustrates a structure of an organic light emitting device wherea substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 aresequentially laminated. In the aforementioned structure, the compoundmay be included in the light emitting layer 3.

FIG. 2 illustrates a structure of an organic light emitting device wherethe substrate 1, the anode 2, a hole injection layer 5, a hole transportlayer 6, a light emitting layer 7, an electron transport layer 8, andthe cathode 4 are sequentially laminated. In the aforementionedstructure, the compound may be included in one or more layers of thehole injection layer 5, the hole transport layer 6, the light emittinglayer 7, and the electron transport layer 8.

The organic light emitting device of the present specification may bemanufactured by a material and a method known in the art, except thatone or more layers of organic material layers include the compound ofthe present specification, that is, the heterocyclic compound or thecompound in which the heat-curable or photo-curable functional group isintroduced into the heterocyclic compound.

For example, the organic light emitting device of the presentspecification may be manufactured by sequentially laminating the firstelectrode, the organic material layer, and the second electrode on thesubstrate. In this case, the organic light emitting device may bemanufactured by depositing metal, metal oxides having conductivity, oran alloy thereof on the substrate by using a PVD (physical vapordeposition) method such as a sputtering method or an e-beam evaporationmethod to form the anode, forming the organic material layer includingthe hole injection layer, the hole transport layer, the light emittinglayer, and the electron transport layer thereon, and then depositing amaterial that can be used as the cathode thereon. In addition to thismethod, the organic light emitting device may be manufactured bysequentially depositing a cathode material, the organic material layer,and an anode material on the substrate.

Further, the heterocyclic compound may be formed into the organicmaterial layer by a solution coating method as well as a vacuumdeposition method when the organic light emitting device ismanufactured. Herein, the solution coating method means spin coating,dip coating, doctor blading, inkjet printing, screen printing, a spraymethod, roll coating, or the like, but is not limited thereto.

The substrate may be selected in consideration of optical and physicalproperties, if necessary. For example, it is preferable that thesubstrate be transparent. A hard material may be used in the substrate,but the substrate may be formed of a flexible material such as plastic.

Examples of the material of the substrate may include, in addition toglass and quartz, PET (polyethylene terephthalate), PEN (polyethylenenaphthalate), PP (polypropylene), PI (polyimide), PC (polycarbonate), PS(polystyrene), POM (polyoxymethylene), an AS resin (acrylonitrilestyrene copolymer), an ABS resin (acrylonitrile butadiene styrenecopolymer), TAC (triacetyl cellulose), PAR (polyarylate), and the like,but are not limited thereto.

It is preferable that the cathode material be, in general, a materialhaving a small work function so as to easily inject electrons into theorganic material layer. Specific examples of the cathode materialinclude metals such as magnesium, calcium, sodium, potassium, titanium,indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead,or an alloy thereof; a multilayered structure material such as LiF/Al orLiO₂/Al, and the like, but are not limited thereto.

It is preferable that the anode material be, in general, a materialhaving a large work function so as to smoothly inject holes into theorganic material layer. Specific examples of the anode material that canbe used in the present specification include metals such as vanadium,chrome, copper, zinc, and gold, or an alloy thereof; metal oxides suchas zinc oxides, indium oxides, indium tin oxides (ITO), and indium zincoxides (IZO); a combination of metal and oxide, such as ZnO:Al orSnO₂:Sb; conductive polymers such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, andpolyaniline, and the like, but are not limited thereto.

The hole transport layer is a layer receiving the holes from the holeinjection layer and transporting the holes to the light emitting layer,the hole transport material is a material capable of receiving the holesfrom the anode or the hole injection layer and transporting the holes tothe light emitting layer, and a material having large mobility of theholes is suitable. Specific examples thereof include an arylamine-basedorganic material, a conductive polymer, a block copolymer in which aconjugate portion and a non-conjugate portion are present together, andthe like, but are not limited thereto.

The hole injection layer is a layer injecting the holes from theelectrode, and it is preferable that the hole injection material be acompound which has an ability of transporting the holes to have a holeinjection effect in the anode and an excellent hole injection effect tothe light emitting layer or the light emitting material, preventsmovement of an exciton generated in the light emitting layer to theelectron injection layer or the electron injection material, and has anexcellent thin film forming ability. It is preferable that a HOMO(highest occupied molecular orbital) of the hole injection material bebetween the work function of the anode material and a HOMO of aperipheral organic material layer. Specific examples of the holeinjection material include metal porphyrin, oligothiophene, anarylamine-based organic material, a phthalocyanine derivative, ahexanitrilehexaazatriphenylene-based organic material, aquinacridone-based organic material, a perylene-based organic material,anthraquinone, and polyaniline and polythiophene-based conductivepolymers, and the like, but are not limited thereto.

The light emitting material is a material that can receive the holes andthe electrons from the hole transport layer and the electron transportlayer, respectively, and bond the holes and the electrons to emit lightin a visible ray region, and is preferably a material having goodquantum efficiency to fluorescence or phosphorescence. Specific examplesthereof include a 8-hydroxy-quinoline aluminum complex (Alq₃); acarbazole-based compound; a dimerized styryl compound; BAlq; a10-hydroxybenzoquinoline-metal compound; benzoxazole, benzthiazole, andbenzimidazole-based compounds; a poly(p-phenylenevinylene) (PPV)-basedpolymer; a spiro compound; polyfluorene, lubrene, and the like, but arenot limited thereto.

The light emitting layer may include a host material and a dopantmaterial. Examples of the host material include a condensation aromaticcycle derivative, a heterocycle-containing compound, or the like.Specific examples of the compensation aromatic cycle derivative includean anthracene derivative, a pyrene derivative, a naphthalene derivative,a pentacene derivative, a phenanthrene compound, a fluoranthenecompound, and the like, and specific examples of theheterocycle-containing compound include a carbazole derivative, adibenzofuran derivative, a ladder-type furan compound, a pyrimidinederivative, and the like, but the examples are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, astyrylamine compound, a boron complex, a fluoranthene compound, a metalcomplex, and the like. Specifically, the aromatic amine derivative is acompensation aromatic cycle derivative having a substituted orunsubstituted arylamino group, examples thereof include pyrene,anthracene, chrysene, and periflanthene having the arylamino group, andthe like, the styrylamine compound is a compound where at least onearylvinyl group is substituted in substituted or unsubstitutedarylamine, and in the styrylamine compound, one or two or moresubstituent groups selected from the group consisting of an aryl group,a silyl group, an alkyl group, a cycloalkyl group, and an arylaminogroup are substituted or unsubstituted. Specific examples thereofinclude styrylamine, styryldiamine, styryltriamine, styryltetramine, andthe like, but are not limited thereto. Further, examples of the metalcomplex include an iridium complex, a platinum complex, and the like,but are not limited thereto.

The electron injection layer is a layer injecting the electrons from theelectrode, and a compound which has an ability of transporting theelectrons, an electron injection effect from the cathode, and anexcellent electron injection effect to the light emitting layer or thelight emitting material, prevents movement of an exciton generated inthe light emitting layer to the hole injection layer, and has anexcellent thin film forming ability is preferable. Specific examplesthereof include fluorenone, anthraquinodimethane, diphenoquinone,thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like,and derivatives thereof, a metal complex compound, a nitrogen-containing5-membered cycle derivative, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)beryllium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium,bis(2-methyl-8-quinolinato)(o-cresolato)gallium,bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum,bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but arenot limited thereto.

The electron transport layer is a layer receiving the electrons from theelectron injection layer and transporting the electrons to the lightemitting layer, the electron transport material is a material that canreceive the electrons well from the cathode and transport the electronsto the light emitting layer, and a material having large mobility of theelectrons is suitable. Specific examples thereof include an8-hydroxyquinoline Al complex; a complex including Alq₃; an organicradical compound; a hydroxyflavone-metal complex, and the like, but arenot limited thereto.

The hole blocking layer is a layer blocking arrival of the holes at thecathode, and in general, may be formed under the same condition as thehole injection layer. Specific examples thereof include an oxadiazolederivative, a triazole derivative, a phenanthroline derivative, BCP, analuminum complex, and the like, but are not limited thereto.

In the exemplary embodiment of the present specification, the organiclight emitting device may be a top emission type, a bottom emissiontype, or a both-sided emission type according to the used material.

A method of synthesizing the organic compound represented by ChemicalFormula 1 or Chemical Formula 2 and manufacturing of the organic lightemitting device using the same will be described in more detail by thefollowing Examples and Comparative Examples. However, the Examples areset to illustrate the present specification but are not to be construedto limit the scope of the present specification.

Preparation Example 1

1) Preparation of Structural Formula A-1

9-(2-bromophenyl)-carbazole (20.9 g, 62.1 mmol) was dissolved inanhydrous tetrahydrofuran (THF) (200 ml) and then cooled to −78° C. 2.5Mn-butyllithium (n-Bu-Li) (24.8 ml, 62.1 mmol) was added for 30 minutesand then agitated at −78° C. for 2 hours. After2,4-diphenyl-indeno[1,2-d]pyrimidine-5-one (18.9 g, 56.4 mmol) was addedat −78° C., the temperature was increased to normal temperature, and thereaction was quenched by the ammonium chloride aqueous solution (aq.NH₄Cl). After the organic layer was separated, concentration wasperformed and purification was performed by the chromatography to obtainStructural Formula A-1 (15 g, 26 mmol).

FIG. 3 is a view illustrating an MS spectrum of Structural Formula A-1.

2) Preparation of Chemical Formula 1-3

After Structural Formula A-1 (15 g, 26 mmol) obtained in theaforementioned reaction was dissolved in the acetic acid (200 ml), 1 gof the concentrated sulfuric acid (H₂SO₄) was added. After reflux for 24hours, cooling to normal temperature was performed. Water (H₂O) (500 ml)was added to generate the solid. After filtration, the solid waspurified by the chromatography to obtain Chemical Formula 1-3 (6.5 g,yield 45%).

MS: [M+H]⁺=560

FIG. 4 is a view illustrating an MS spectrum of a compound of ChemicalFormula 1-3.

Preparation Example 2

1) Preparation of Structural Formula B-1

9-(2-bromophenyl)-carbazole (20.9 g, 62.1 mmol) was dissolved inanhydrous tetrahydrofuran (THF) (200 ml) and then cooled to −78° C. 2.5Mn-butyllithium (n-Bu-Li) (24.8 ml, 62.1 mmol) was added for 30 minutesand then agitated at −78° C. for 2 hours. After Structural Formula B(18.9 g, 56.4 mmol) was added at −78° C., the temperature was increasedto normal temperature, and the reaction was quenched by the ammoniumchloride aqueous solution (aq. NH₄Cl). After the organic layer wasseparated, concentration was performed and purification was performed bythe chromatography to obtain Structural Formula B-1 (17.3 g, yield 52%).

2) Preparation of Chemical Formula 1-4

After Structural Formula B-1 (17.3 g, 29.9 mmol) obtained in theaforementioned reaction was dissolved in acetic acid (200 ml), 1 g ofthe concentrated sulfuric acid (H₂SO₄) was added. After reflux for 24hours, cooling to normal temperature was performed. Water (H₂O) (500 ml)was added to generate a solid. After filtration, the solid was purifiedby the chromatography to obtain Chemical Formula 1-4 (5.5 g, yield 33%).

MS: [M+H]⁺=560

Preparation Example 3

1) Preparation of Structural Formula C-1

9-(2-bromophenyl)-carbazole (10 g, 31.0 mmol) was dissolved in anhydroustetrahydrofuran (THF) (200 ml) and then cooled to −78° C. 2.5Mn-butyllithium (n-Bu-Li) (12.4 ml, 31.0 mmol) was added for 30 minutesand then agitated at −78° C. for 2 hours. After Structural Formula C(7.3 g, 28.2 mmol) was added at −78° C., the temperature was increasedto normal temperature, and the reaction was quenched by the ammoniumchloride aqueous solution (aq. NH₄Cl). After the organic layer wasseparated, concentration was performed and purification was performed bythe chromatography to obtain Structural Formula C-1 (5.8 g, yield 41%).

2) Preparation of Chemical Formula 1-1

After Structural Formula C-1 (5.8 g, 11.6 mmol) obtained in theaforementioned reaction was dissolved in the acetic acid (100 ml), 1 gof the concentrated sulfuric acid (H₂SO₄) was added. After reflux for 24hours, cooling to normal temperature was performed. Water (H₂O) (500 ml)was added to generate the solid. After filtration, the solid waspurified by the chromatography to obtain Chemical Formula 1-1 (2.9 g,yield 52%).

MS: [M+H]⁺=483

Preparation Example 4

1) Preparation of Structural Formula D-1

9-(2-bromophenyl)-carbazole (10 g, 31.0 mmol) was dissolved in anhydroustetrahydrofuran (THF) (200 ml) and then cooled to −78° C. 2.5Mn-butyllithium (n-Bu-Li) (12.4 ml, 31.0 mmol) was added for 30 minutesand then agitated at −78° C. for 2 hours. After Structural Formula D(7.3 g, 28.2 mmol) was added at −78° C., the temperature was increasedto normal temperature, and the reaction was quenched by the ammoniumchloride aqueous solution (aq. NH₄Cl). After the organic layer wasseparated, concentration was performed and purification was performed bythe chromatography to obtain Structural Formula D-1 (6.1 g, yield 43%).

2) Preparation of Chemical Formula 1-2

After Structural Formula D-1 (5.8 g, 12.2 mmol) obtained in theaforementioned reaction was dissolved in the acetic acid (100 ml), 1 gof the concentrated sulfuric acid (H₂SO₄) was added. After reflux for 24hours, cooling to normal temperature was performed. Water (H₂O) (500 ml)was added to generate the solid. After filtration, the solid waspurified by the chromatography to obtain Chemical Formula 1-2 (2.5 g,yield 45%).

MS: [M+H]⁺=483

Preparation Example 5

1) Preparation of Structural Formula E-1

9-(2-bromophenyl)-carbazole (15 g, 46.5 mmol) was dissolved in anhydroustetrahydrofuran (THF) (200 ml) and then cooled to −78° C. 2.5Mn-butyllithium (n-Bu-Li) (18.6 ml, 46.5 mmol) was added for 30 minutesand then agitated at −78° C. for 2 hours. After Structural Formula E(14.9 g, 38.8 mmol) was added at −78° C., the temperature was increasedto normal temperature, and the reaction was quenched by the ammoniumchloride aqueous solution (aq. NH₄Cl). After the organic layer wasseparated, concentration was performed and purification was performed bythe chromatography to obtain Structural Formula E-1 (11.7 g, yield 48%).

2) Preparation of Chemical Formula 1-13

After Structural Formula E-1 (11.7 g, 18.6 mmol) obtained in theaforementioned reaction was dissolved in the acetic acid (100 ml), 1 gof the concentrated sulfuric acid (H₂SO₄) was added. After reflux for 24hours, cooling to normal temperature was performed. Water (H₂O) (500 ml)was added to generate the solid. After filtration, the solid waspurified by the chromatography to obtain Chemical Formula 1-13 (4.1 g,yield 36%).

MS: [M+H]⁺=609

Preparation Example 6

1) Preparation of Structural Formula F-1

9-(2-bromophenyl)-carbazole (10 g, 31.0 mmol) was dissolved in anhydroustetrahydrofuran (THF) (200 ml) and then cooled to −78° C. 2.5Mn-butyllithium (n-Bu-Li) (12.4 ml, 31.0 mmol) was added for 30 minutesand then agitated at −78° C. for 2 hours. After Structural Formula F(12.5 g, 25.8 mmol) was added at −78° C., the temperature was increasedto normal temperature, and the reaction was quenched by the ammoniumchloride aqueous solution (aq. NH₄Cl). After the organic layer wasseparated, concentration was performed and purification was performed bythe chromatography to obtain Structural Formula F-1 (11.1 g, yield 59%).

2) Preparation of Chemical Formula 1-11

After Structural Formula F-1 (11.1 g, 15.2 mmol) obtained in theaforementioned reaction was dissolved in the acetic acid (100 ml), 1 gof the concentrated sulfuric acid (H₂SO₄) was added. After reflux for 24hours, cooling to normal temperature was performed. Water (H₂O) (500 ml)was added to generate the solid. After filtration, the solid waspurified by the chromatography to obtain Chemical Formula 1-11 (5.7 g,yield 53%).

MS: [M+H]⁺=711

Preparation Example 7

1) Preparation of Structural Formula G-1

9-(2-bromophenyl)-carbazole (10 g, 31.0 mmol) was dissolved in anhydroustetrahydrofuran (THF) (200 ml) and then cooled to −78° C. 2.5Mn-butyllithium (n-Bu-Li) (12.4 ml, 31.0 mmol) was added for 30 minutesand then agitated at −78° C. for 2 hours. After Structural Formula G(13.8 g, 25.8 mmol) was added at −78° C., the temperature was increasedto normal temperature, and the reaction was quenched by the ammoniumchloride aqueous solution (aq. NH₄Cl). After the organic layer wasseparated, concentration was performed and purification was performed bythe chromatography to obtain Structural Formula G-1 (5.2 g, yield 26%).

2) Preparation of Chemical Formula 1-19

After Structural Formula G-1 (5.2 g, 6.7 mmol) obtained in theaforementioned reaction was dissolved in acetic acid (50 ml), 0.1 g ofconcentrated sulfuric acid (H₂SO₄) was added. After reflux for 24 hours,cooling to normal temperature was performed. Water (H₂O) (200 ml) wasadded to generate the solid. After filtration, the solid wasrecrystallized by using ethyl acetate and hexane to obtain ChemicalFormula 1-19 (2.8 g, yield 56%).

MS: [M+H]⁺=759

Preparation Example 8

1) Preparation of Structural Formula H-1

Structural Formula H (15 g, 46.3 mmol) was dissolved in anhydroustetrahydrofuran (THF) (200 ml) and then cooled to −78° C. 2.5Mn-butyllithium (n-Bu-Li) (18.5 ml, 46.3 mmol) was added for 30 minutesand then agitated at −78° C. for 2 hours. After2,4-diphenyl-indeno[1,2-d]pyrimidine-5-one (12.9 g, 38.6 mmol) was addedat −78° C., the temperature was increased to normal temperature, and thereaction was quenched by the ammonium chloride aqueous solution (aq.NH₄Cl). After the organic layer was separated, concentration wasperformed and purification was performed by the chromatography to obtainStructural Formula H-1 (14.1 g, yield 63%).

2) Preparation of Chemical Formula 2-3

After Structural Formula H-1 (14.1 g, 24.3 mmol) obtained in theaforementioned reaction was dissolved in acetic acid (150 ml), 1 g ofconcentrated sulfuric acid (H₂SO₄) was added. After reflux for 24 hours,cooling to normal temperature was performed. Water (H₂O) (500 ml) wasadded to generate the solid. After filtration, the solid was purified bythe chromatography to obtain Chemical Formula 2-3 (6.4 g, yield 47%).

MS: [M+H]⁺=561

Example 1 Light Emitting Layer

A glass substrate on which a thin film of ITO (indium tin oxide) wasapplied in a thickness of 500 Å was put into distilled water having thedetergent dissolved therein and washed by the ultrasonic wave. In thiscase, the product manufactured by Fischer Co., was used as thedetergent, and distilled water, which had been twice filtered by thefilter manufactured by Millipore Co., was used as the distilled water.The ITO was washed for 30 minutes, and washing with ultrasonic waves wasthen repeated twice for 10 minutes using distilled water. After thewashing with distilled water was finished, washing with ultrasonic waveswas performed by solvents such as isopropyl alcohol, acetone, andmethanol, and the ITO was dried and transported to the plasma washingmachine. Further, the substrate was washed by using oxygen plasma for 5minutes, and then transported to the vacuum deposition machine.

Hexanitrile hexaazatriphenylene (HAT) of the following Chemical Formulawas thermally deposited under vacuum in a thicknesses of 500 Å on theITO transparent electrode thus prepared to form a hole injection layer.

4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (250 Å),hexanitrile hexaazatriphenylene (HAT) (50 Å), and4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å) of theaforementioned Chemical Formulas were sequentially deposited undervacuum on the hole injection layer to form a hole transport layer.

Subsequently, the manufactured compound of Chemical Formula 1-3 and adopant compound GD as illustrated below were deposited under vacuum at aweight ratio of 10:1 in a film thickness of 300 Å on the hole transportlayer to form a light emitting layer.

The compound of Chemical Formula ET-A and the aforementioned ChemicalFormula LiQ (lithium quinalate) were deposited under vacuum as theelectron transport layer material at a weight ratio of 1:1 on the lightemitting layer to form an electronic injection and transport layer in athickness of 300 Å.

Lithium fluoride (LiF) in a thickness of 15 Å and aluminum in athickness of 1,000 Å were subsequently deposited on the electroninjection and transport layer to form a cathode.

In the aforementioned process, the deposition speed of the organicmaterial was maintained at 0.4 to 0.7 Å/sec, the deposition speed oflithium fluoride of the cathode was maintained at 0.3 Å/sec, thedeposition speed of aluminum was maintained at 2 Å/sec, and the degreeof vacuum during deposition was maintained at 2×10⁻⁷ to 5×10⁻⁸ torr tomanufacture an organic light emitting device.

Example 2 Light Emitting Layer

An organic light emitting device was manufactured by the same method asExample 1, except that the prepared compound of Chemical Formula 1-4 wasused instead of the compound of Chemical Formula 1-3 of Example 1.

Example 3 Light Emitting Layer

An organic light emitting device was manufactured by the same method asExample 1, except that the prepared compound of Chemical Formula 1-1 wasused instead of the compound of Chemical Formula 1-3 of Example 1.

Example 4 Light Emitting Layer

An organic light emitting device was manufactured by the same method asExample 1, except that the prepared compound of Chemical Formula 1-2 wasused instead of the compound of Chemical Formula 1-3 of Example 1.

Example 5 Light Emitting Layer

An organic light emitting device was manufactured by the same method asExample 1, except that the prepared compound of Chemical Formula 1-13was used instead of the compound of Chemical Formula 1-3 of Example 1.

Example 6 Light Emitting Layer

An organic light emitting device was manufactured by the same method asExample 1, except that the prepared compound of Chemical Formula 1-11was used instead of the compound of Chemical Formula 1-3 of Example 1.

Example 7 Light Emitting Layer

An organic light emitting device was manufactured by the same method asExample 1, except that the prepared compound of Chemical Formula 1-19was used instead of the compound of Chemical Formula 1-3 of Example 1.

Example 8 Light Emitting Layer

An organic light emitting device was manufactured by the same method asExample 1, except that the prepared compound of Chemical Formula 2-3 wasused instead of the compound of Chemical Formula 1-3 of Example 1.

Comparative Example 1

An organic light emitting device was manufactured by the same method asExample 1, except that the compound of the following Chemical FormulaGH-A was used instead of the compound of Chemical Formula 1-9 of Example1.

When the current (10 mA/cm²) was applied to the organic light emittingdevices manufactured in the Examples and Comparative Example 1, theresults of the following Table 1 were obtained.

TABLE 1 Voltage Efficiency Compound (V) (cd/A) Example 1 ChemicalFormula 1-3 4.65 67.5 Example 2 Chemical Formula 1-4 4.80 69.2 Example 3Chemical Formula 1-1 4.93 58.6 Example 4 Chemical Formula 1-2 4.95 57.7Example 5 Chemical Formula 1-13 4.21 40.6 Example 6 Chemical Formula1-11 4.60 67.7 Example 7 Chemical Formula 1-19 4.10 58.3 Example 8Chemical Formula 2-3 4.10 65.2 Comparative GH-A 6.12 15.26 Example 1

From the results of Table 1, it can be seen that the new compoundaccording to the present invention may be used as a material of a lightemitting layer of an organic electronic device including an organiclight emitting device, and the organic electronic device including theorganic light emitting device using the same exhibits excellentproperties in views of efficiency, driving voltage, stability and thelike. Particularly, the compound may reduce the driving voltage andinduce an increase in efficiency to improve power consumption.

What is claimed is:
 1. A heterocyclic compound represented by thefollowing Chemical Formula 1 or 2:

wherein a is an integer of 0 to 7, b is an integer of 0 to 4, c is aninteger of 0 to 8, d is an integer of 0 to 5, A₁ to A₈ are the same asor different from each other and are each independently CR or N, but twoor more of A₁ to A₈ are N, and R and R₁ to R₄ are the same as ordifferent from each other, and are each independently hydrogen;deuterium; a halogen group; a nitrile group; a nitro group; a hydroxygroup; a carbonyl group; an ester group; an imide group; an amide group;a substituted or unsubstituted alkyl group; a substituted orunsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted silyl group;a substituted or unsubstituted boron group; a substituted orunsubstituted alkylamine group; a substituted or unsubstitutedaralkylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted heteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heterocyclic group including one or more ofN, O, and S atoms.
 2. The heterocyclic compound of claim 1, wherein twoor more of A₅ to A₈ are N.
 3. The heterocyclic compound of claim 1,wherein A₅ and A₇ are N, A₆ and A₈ are CR or A₆ and A₈ are N, and A₅ andA₇ are CR.
 4. The heterocyclic compound of claim 1, wherein R ishydrogen; a substituted or unsubstituted aryl group; or a substituted orunsubstituted heterocyclic group including one or more of N, O, and Satoms.
 5. The heterocyclic compound of claim 1, wherein R is hydrogen;an aryl group unsubstituted or substituted with one or two or moresubstituent groups selected from the group consisting of the substitutedor unsubstituted phosphine oxide group, the substituted or unsubstitutedaryl group, and the substituted or unsubstituted heterocyclic groupincluding one or more of the N, O, and S atoms; or a heterocyclic groupincluding one or more of N, O, and S atoms unsubstituted or substitutedwith one or two or more substituent groups selected from the groupconsisting of the substituted or unsubstituted phosphine oxide group,the substituted or unsubstituted aryl group, and the substituted orunsubstituted heterocyclic group including one or more of the N, O, andS atoms.
 6. The heterocyclic compound of claim 1, wherein theheterocyclic compound represented by Chemical Formula 1 is representedby any one of the following Chemical Formulas 1-1 to 1-36:


7. The heterocyclic compound of claim 1, wherein the heterocycliccompound represented by Chemical Formula 2 is represented by any one ofthe following Chemical Formulas 2-1 to 2-32:


8. An organic light emitting device comprising: a first electrode; asecond electrode; and organic material layers formed of one or morelayers including a light emitting layer disposed between the firstelectrode and the second electrode, wherein one or more layers of theorganic material layers include the heterocyclic compound according toany one of claims 1 to 7, or a compound in which a heat-curable orphoto-curable functional group is introduced into the heterocycliccompound.
 9. The organic light emitting device of claim 8, wherein theorganic material layer includes a hole transport layer, a hole injectionlayer, or a layer where both hole transporting and hole injection areperformed, and the hole transport layer, the hole injection layer, orthe layer where both the hole transporting and the hole injection areperformed includes the heterocyclic compound or the compound in whichthe heat-curable or photo-curable functional group is introduced intothe heterocyclic compound.
 10. The organic light emitting device ofclaim 8, wherein the organic material layer includes an electroninjection layer, and the electron injection layer includes theheterocyclic compound or the compound in which the heat-curable orphoto-curable functional group is introduced into the heterocycliccompound.
 11. The organic light emitting device of claim 8, wherein theorganic material layer includes an electron transport layer, and theelectron transport layer includes the heterocyclic compound or thecompound in which the heat-curable or photo-curable functional group isintroduced into the heterocyclic compound.
 12. The organic lightemitting device of claim 8, wherein the light emitting layer includesthe heterocyclic compound or the compound in which the heat-curable orphoto-curable functional group is introduced into the heterocycliccompound.
 13. The organic light emitting device of claim 8, wherein theorganic material layer includes the heterocyclic compound or thecompound in which the heat-curable or photo-curable functional group isintroduced into the heterocyclic compound as a host, and another organiccompound, a metal, or a metal compound as a dopant.
 14. The organiclight emitting device of claim 8, wherein the heat-curable orphoto-curable functional group is a vinyl group or an acryl group. 15.The organic light emitting device of claim 8, wherein the organicmaterial layer further includes one layer or two or more layers selectedfrom the group consisting of a hole injection layer, a hole transportlayer, an electron transport layer, an electron injection layer, anelectron blocking layer, and a hole blocking layer.